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Synthesis 2008(17): 2776-2797
DOI: 10.1055/s-2008-1067225
DOI: 10.1055/s-2008-1067225
SPECIALTOPIC
© Georg Thieme Verlag
Stuttgart ˙ New YorkPd-NHC (PEPPSI) Complexes: Synthetic Utility and Computational Studies into Their Reactivity
Further Information
Received
1 July 2008
Publication Date:
13 August 2008 (online)
Publication History
Publication Date:
13 August 2008 (online)
Abstract
This review concentrates on the results obtained thus far in cross-coupling reactions utilising Pd-PEPPSI-IPr (pre)catalyst. Results from computational studies expose possible factors behind the high reactivity of this complex, as well as mechanistic details for the IPr-Pd-mediated alkyl-alkyl Negishi cross-coupling.
1 Introduction
2 Evolution to Pd-PEPPSI Complexes
2.1 Background of NHCs; Unraveling Electronic and Steric Components
2.2 Design and Preparation of Pd-PEPPSI Complexes
2.3 Mechanism of Activation and Role in the Catalytic Cycle
3 Cross-Coupling Results with Pd-PEPPSI Complexes
3.1 General Cross-Coupling Scheme
3.2 The Suzuki-Miyaura Reaction
3.3 The Kumada-Tamao-Corriu Reaction
3.4 The Negishi Reaction
3.5 Buchwald-Hartwig-Yagupol’skii Amination
4 Theory and Computation
4.1 Theory
4.2 Computation
4.3 Geometric Structure
4.4 Reaction Profile
4.5 Interactions
4.6 Atoms-in-Molecules
5 Conclusions
Key words
palladium - cross-coupling - PEPPSI - computation
- 1
Herrmann WA. Angew. Chem. Int. Ed. 2002, 41: 1290Reference Ris Wihthout Link - 2
Kantchev EAB.O’Brien CJ.Organ MG. Angew. Chem. Int. Ed. 2007, 46: 2768 - 3
Kantchev EAB.O’Brien CJ.Organ MG. Aldrichimica Acta 2006, 39: 97 - 4
Herrmann WA.Öfele K.Preysing D.-v.Schneider SK. J. Organomet. Chem. 2003, 687: 229 - 5
O’Brien CJ.Kantchev EAB.Valente C.Hadei N.Chass GA.Lough A.Hopkinson AC.Organ MG. Chem. Eur. J. 2006, 12: 4743 - 6
Valente C.Baglione S.Candito D.O’Brien CJ.Organ MG. Chem. Commun. 2008, 735 - 7
Organ MG.Avola S.Dubovyk I.Hadei N.Kantchev EAB.O’Brien CJ.Valente C. Chem. Eur. J. 2006, 12: 4749 - 8
Organ MG.Abdel-Hadi M.Avola S.Hadei N.Nasielski J.O’Brien CJ.Valente C. Chem. Eur. J. 2007, 13: 150 - 9
Organ MG.Abdel-Hadi M.Avola S.Dubovyk I.Hadei N.Kantchev EAB.O’Brien CJ.Valente C. Chem. Eur. J. 2008, 14: 2443 - 10
Wanzlick H.-W.Schönherr H.-J. Angew. Chem., Int. Ed. Engl. 1968, 7: 141Reference Ris Wihthout Link - 11
Öfele K. J. Organomet. Chem. 1968, 12: P42Reference Ris Wihthout Link - 12
Arduengo AJ.Harlow RL.Kline M. J. Am. Chem. Soc. 1991, 113: 361Reference Ris Wihthout Link - 13
Nair V.Bindu S.Sreekumar V. Angew. Chem. Int. Ed. 2004, 43: 5130 - 14
Perry MC.Burgess K. Tetrahedron: Asymmetry 2003, 14: 951 - 15
Crudden CM.Allen DP. Coord. Chem. Rev. 2004, 248: 2247Reference Ris Wihthout Link - 16
Nolan SP.Scott NM. Eur. J. Inorg. Chem. 2005, 1815 - 17
Crabtree RH. J. Organomet. Chem. 2005, 690: 5451 - 18
Youngs WJ.Garrison JC. Chem. Rev. 2005, 105: 3978 - 19
Cavallo L.Correa A.Costabile C.Jacobsen H. J. Organomet. Chem. 2005, 690: 5407Reference Ris Wihthout Link - 20
Herrmann WA.Fischer EJ.Köchter C.Arthus GRJ. Angew. Chem., Int. Ed. Engl. 1995, 107: 2602 - 21
Herrmann WA.Mihalios D.Öfele K.Kiprof P.Belmedjahed F. Chem. Ber. 1992, 125: 1795 - 22
Öfele K.Herrmann WA.Mihalios D.Elison M.Herdtweck E.Scherer W.Mink J. J. Organomet. Chem. 1993, 459: 177 - 23
Herrmann WA.Öfele K.Elison M.Kuhn FE.Roesky PW. J. Organomet. Chem. 1994, 480: C7 - 24
Littke AF.Fu GC. Angew. Chem. Int. Ed. 2002, 41: 4176Reference Ris Wihthout Link - 25
Cárdenas DJ. Angew. Chem. Int. Ed. 1999, 38: 3018 - 26
Netherton MR.Fu GC. Adv. Synth. Catal. 2004, 346: 1525 - 27
Frisch AC.Beller M. Angew. Chem. Int. Ed. 2005, 44: 674Reference Ris Wihthout Link - 28
Valentine DHJ.Hillhouse JH. Synthesis 2003, 2437 - 29
Dias PB.Piedade MEM.Simões JAM. Coord. Chem. Rev. 1994, 135-136: 737 - 30
Tolman CA. Chem. Rev. 1977, 77: 313Reference Ris Wihthout Link - 31
Mauger CC.Mignani GA. Aldrichimica Acta 2006, 39: 17 - 32
Amyes TL.Diver ST.Richard JP.Rivas FM.Toth K. J. Am. Chem. Soc. 2004, 126: 4366 - 33
Frohlich N.Pindun U.Stahl M.Frenking G. Organometallics 1997, 16: 442 - 34
Chen H.Justes DR.Cooks RG. Org. Lett. 2005, 7: 3949 - 35
Cowley AH. J. Organomet. Chem. 2001, 617-618: 105 - 36
Chianese AR.Li X.Janzen MC.Faller JW.Crabtree RH. Organometallics 2003, 22: 1663Reference Ris Wihthout Link - 37
Dorta R.Stevens ED.Scott NM.Costabile C.Cavallo L.Hoff CD.Nolan SP. J. Am. Chem. Soc. 2004, 127: 2485 - 38
Herrmann WA.Schütz J.Frey GD.Herdtweck E. Organometallics 2006, 25: 2437 - 39
O’Brien CJ.Kantchev EAB.Chass GA.Hadei N.Hopkinson AC.Organ MG.Setiadi DH.Tang T.-H.Fang D.-C. Tetrahedron 2005, 61: 9723 - 40
Culkin DA.Hartwig JF. Organometallics 2004, 23: 3398 - 41
Mann G.Shelby Q.Roy AH.Hartwig JF. Organometallics 2003, 22: 2775 - 42
Page PCB.Buckley BR.Christie SDR.Edgar M.Poulton AM.Elsegood MRJ.McKee VJ. J. Organomet. Chem. 2005, 690: 6210 - 43
Lebel H.Janes MK.Charette AB.Nolan SP. J. Am. Chem. Soc. 2004, 126: 5046 - 44
Ma Y.Song C.Jiang W.Xue G.Cannon JF.Wang X.Andrus MB. Org. Lett. 2003, 5: 4635Reference Ris Wihthout Link - 45
Love JA.Morgan JP.Trnka TM.Grubbs RG. Angew. Chem. Int. Ed. 2002, 41: 4035Reference Ris Wihthout Link - 46
Hall DG. Boronic Acids: Preparation Applications in Organic Synthesis and Medicine Wiley-VCH; Weinheim: 2005. - 47
Thomas SE. Organic synthesis: the roles of boron and silicon Oxford University Press; Oxford: 1991. - 48
de Meijere A.Diederich F. Metal-catalyzed cross-coupling reactions 2nd ed.:Miyarua N. Wiley-VCH; Weinheim: 2004. p.41-123 - 49
Chemler SR.Trauner D.Danishefsky SJ. Angew. Chem. Int. Ed. 2001, 40: 4544 - 50
Negishi E.-i. Aspects of Mechanism and Organometallic ChemistryBrewster JH. Plenum; New York: 1978. p.285 - 51
Negishi E.-i. J. Organomet. Chem. 2002, 653: 34 - 52
Miyaura N.Yamada K.Suzuki A. Tetrahedron Lett. 1979, 20: 3437 - 53
Miyarua N.Suzuki A. J. Chem. Soc. Chem. Commun. 1979, 866 - 54
Bellina F.Carpita A.Rossie R. Synthesis 2004, 2419 - 55
Miura M. Angew. Chem. Int. Ed. 2004, 43: 2201 - 56
Miyaura N. Top. Curr. Chem. 2002, 219: 11 - 57
Suzuki A. J. Organomet. Chem. 1999, 576: 147Reference Ris Wihthout Link - 58
Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457Reference Ris Wihthout Link - 59
Herrmann WA.Reisinger C.-P.Spiegler M. J. Organomet. Chem. 1998, 557: 93 - 60
Zhang C.Huang J.Trudell ML.Nolan SP. J. Org. Chem. 1999, 64: 3804 - 61
Andrus MB.Song C. Org. Lett. 2001, 3: 3761 - 62
Gstöttmayr CWK.Böhm VPW.Herdtweck E.Grosche M.Herrmann WA. Angew. Chem. Int. Ed. 2002, 41: 1363 - 63
Altenhoff G.Goddard R.Lehmann CW.Glorius F. Angew. Chem. Int. Ed. 2003, 42: 3690 - 64
Navarro O.Kelly RA.Nolan SP. J. Am. Chem. Soc. 2003, 125: 16194 - 65
Song C.Ma Y.Chai Q.Ma C.Jiang W.Andrus MB. Tetrahedron 2005, 61: 7438 - 66
Altenhoff G.Goddard R.Lehmann CW.Glorius F. J. Am. Chem. Soc. 2004, 126: 15195 - 67
Navarro O.Kaur H.Mahjoor P.Nolan SP. J. Org. Chem. 2004, 69: 3173Reference Ris Wihthout Link - 68
Cesar V.Bellemin-Laponnaz S.Gade LH. Organometallics 2002, 21: 5204 - 69
Palencia H.Garcia-Jimenez F.Takacs JM. Tetrahedron Lett. 2004, 45: 3849 - 70
Schneider SK.Herrmann WA.Herdtweck E. J. Mol. Catal. 2006, 245: 248 - 71
Fuller AA.Hester HR.Salo EV.Stevens EP. Tetrahedron Lett. 2003, 44: 2935Reference Ris Wihthout Link - 72
Abraham MH.Grellier PL. The Chemistry of the Metal-Carbon BondHartley FR.Patai S. Wiley; New York: 1985. p.25 - 73
McDougal NT.Schaus SE. J. Am. Chem. Soc. 2003, 125: 12094 - 74
McDougal NT.Trevellini WL.Rodgen SA.Kliman LT.Schaus SE. Adv. Synth. Catal. 2004, 346: 1231 - 75
Perkins JR.Carter RG. J. Am. Chem. Soc. 2008, 130: 3290 - 76
Littke AF.Dai C.Fu GC. J. Am. Chem. Soc. 2000, 122: 4020 - 77
Barder TE.Walker SD.Martinelli JR.Buchwald SL. J. Am. Chem. Soc. 2005, 127: 4749 - 78
Arentsen K.Caddick S.Cloke FGN.Herring AP.Hitchcock PB. Tetrahedron Lett. 2004, 45: 3511Reference Ris Wihthout Link - 79
Singh R.Viciu MS.Kramareva N.Navarro O.Nolan SP. Org. Lett. 2005, 7: 1829 - 80
Tamao K.Sumitani K.Kumada M. J. Am. Chem. Soc. 1972, 94: 4374 - 81
Corriu RJP.Masse JP. Chem. Commun. 1972, 144 - 82
Yamamura M.Moritani I.Murahashi S. J. Organomet. Chem. 1975, 61: C39 - 83
Huang J.Nolan SP. J. Am. Chem. Soc. 1999, 121: 9889Reference Ris Wihthout Link - 84
Frisch AC.Rataboul F.Zapf A.Beller M. J. Organomet. Chem. 2003, 687: 403Reference Ris Wihthout Link - 85
Frisch AC.Zapf A.Briel O.Kayser B.Shaikh N.Beller M. J. Mol. Catal. 2004, 214: 231 - 86
Negishi E.-i.King AO.Okukado N. J. Org. Chem. 1977, 42: 1821Reference Ris Wihthout Link - 87
King AO.Okukado N.Negishi E.-i. Chem. Commun. 1977, 683 - 88
Knochel P.Jones P. Organozinc Reagents - A Practical Approach Oxford University Press; Oxford: 1999. - 89
Iyer S.Jayanthi A. Synlett 2003, 1125 - 90
Zhou J.Fu GC. J. Am. Chem. Soc. 2003, 125: 12527Reference Ris Wihthout Link - 91
Zhu L.Wehmeyer RM.Rieke RD. J. Org. Chem. 1991, 56: 1445 - 92
Rieke RD.Hanson MV.Brown JD.Niu QJ. J. Org. Chem. 1996, 61: 2726 - 93
Hadei N.Kantchev EAB.O’Brien CJ.Organ MG. Org. Lett. 2005, 7: 3805 - 94
Hou S. Org. Lett. 2003, 5: 423 - 95
Kosugi M.Kameyama M.Migita T. Chem. Lett. 1983, 927 - 96
Boger DL.Panek JS. Tetrahedron Lett. 1984, 25: 3175 - 97
Kondratenko NV.Kolomeitsev AA.Mogilevskaya VO.Varlamova NM.Yagupol’skii LM. J. Org. Chem. USSR (Engl. Transl.) 1986, 22: 1547 ; translated from Zh. Org. Khim. 1986, 22, 1721 (original article submitted March 26, 1985) - 98
Guram AS.Rennels RA.Buchwald SL. Angew. Chem. Int. Ed. 1995, 34: 1348Reference Ris Wihthout Link - 99
Louie J.Hartwig JF. Tetrahedron Lett. 1995, 36: 3609Reference Ris Wihthout Link - 100
Schlummer B.Scholz U. Adv. Synth. Catal. 2004, 346: 1599Reference Ris Wihthout Link - 101
Muci AR.Buchwald SL. Top. Curr. Chem. 2002, 219: 131 - 102
Huang J.Grasa GA.Nolan SP. Org. Lett. 1999, 1: 1307Reference Ris Wihthout Link - 103
Grasa GA.Viciu MS.Huang J.Nolan SP. J. Org. Chem. 2001, 66: 7729Reference Ris Wihthout Link - 104
Viciu MS.Germaneau RF.Navarro O.Stevens ED.Nolan SP. Organometallics 2002, 21: 5470Reference Ris Wihthout Link - 105
Viciu MS.Kissling RM.Stevens ED.Nolan SP. Org. Lett. 2002, 4: 2229Reference Ris Wihthout Link - 106
Viciu MS.Kelly RA.Stevens ED.Naud F.Studer M.Nolan SP. Org. Lett. 2003, 5: 1479Reference Ris Wihthout Link - 107
Navarro O.Marion N.Scott NM.González J.Amoroso D.Bell A.Nolan SP. Tetrahedron 2005, 61: 9716 - 108
Marion N.Navarro O.Mei J.Stevens ED.Scott NM.Nolan SP. J. Am. Chem. Soc. 2006, 128: 4101Reference Ris Wihthout Link - 109
Navarro O.Marion N.Mei J.Nolan SP. Chem. Eur. J. 2006, 12: 5142 - 110
Stauffer SR.Hartwig JF. J. Am. Chem. Soc. 2003, 125: 6977 - 111
Titcomb LR.Caddick S.Cloke FGN.Wilson DJ.McKerrecher D. Chem. Commun. 2001, 1388 - 112
Organ MG.Comer E. Chem. Eur. J. 2005, 11: 7223 - 113
Comer E.Organ MG. J. Am. Chem. Soc. 2005, 127: 8160 - 114
Shore G.Morin S.Mallik D.Organ MG. Chem. Eur. J. 2008, 14: 1351 - 115
Barluenga J.Fernandez MA.Aznar F.Valdes C. Chem. Eur. J. 2005, 11: 2276 - 116
Lerma IC.Cawley MJ.Arentsen K.Scott JS.Pearlson SE.Hayler J.Caddick S. J. Organomet. Chem. 2005, 690: 5841 - 117
Ananikov VP.Musaev DG.Morokuma KJ. J. Am. Chem. Soc. 2002, 124: 2839 - 118
Ananikov VP.Musaev DG.Morokuma KJ. Organometallics 2005, 24: 715 - 119
Chin W.Mons M.Dognon J.-P.Mirasol R.Chass G.Dimicoli I.Piuzzi F.Butz P.Tardivel B.Compagnon I.von Helden G.Meijer G. J. Phys. Chem. A 2005, 109: 5281 - 120
Chass GA.Mirasol RS.Setiadi DH.Tang T.-H.Chin W.Mons M.Dimicoli I.Dognon J.-P.Viskolcz B.Lovas S.Penke B.Csizmadia IG. J. Phys. Chem. A 2005, 109: 5289 - 121
Chass GA.Marai CNJ.Harrison AG.Csizmadia KJ. J. Phys. Chem. A 2002, 106: 9695 - 122
Richardson TB.de Gala S.Crabtree RH.Siegbahn PEM. J. Am. Chem. Soc. 1995, 117: 12875 - 123
Robertson KN.Knop O.Cameron TS. Can. J. Chem. 2003, 81: 727 - 124
Alkorta M.Elguero J.Grabowski SJ. J. Phys. Chem. A 2008, 112: 2721 - 125
Frisch MJ.Trucks GW.Schlegel HB.Scuseria GE.Robb MA.Cheeseman JR.Montgomery JA.Vreven JT.Kudin KN.Burant JC.Millam JM.Iyengar SS.Tomasi J.Barone V.Mennucci B.Cossi M.Scalmani G.Rega N.Petersson GA.Nakatsuji H.Hada MEM.Toyota K.Fukuda R.Hasegawa J.Ishida M.Nakajima T.Honda Y.Kitao O.Nakai H.Klene M.Li X.Knox JE.Hratchian HP.Cross JB.Adamo C.Jaramillo J.Gomperts R.Stratmann RE.Yazyev O.Austin AJ.Cammi R.Pomelli C.Ochterski JW.Ayala PY.Morokuma K.Voth GA.Salvador P.Dannenberg JJ.Zakrzewski VG.Dapprich S.Daniels AD.Strain MC.Farkas O.Malick DK.Rabuck AD.Raghavachari K.Foresman JB.Ortiz JV.Cui Q.Baboul AG.Clifford S.Cioslowski J.Stefanov BB.Liu G.Liashenko A.Piskorz P.Komaromi I.Martin RL.Fox DJ.Keith T.Al-Laham MA.Peng CY.Nanayakkara A.Challacombe M.Gill PMW.Johnson B.Chen W.Wong MW.Gonzalez C.Pople JA. Gaussian 03, revision B.02 Gaussian, Inc.; Pittsburgh (PA): 2003. - 126
Godbout N.Salahub DR.Andzelm J.Wimmer E. Can. J. Chem. 1992, 70: 560 - 127
Becke AD. J. Chem. Phys. 1993, 98: 5648 - 128
Lee C.Yang W.Parr RG. Phys. Rev. B. 1988, 37: 785 - 129
Miertus S.Scrocco E.Tomasi J. Chem. Phys. 1981, 55: 117 - 130
Barone V.Cossi M.Tomasi J. J. Chem. Phys. 1997, 107: 3210 - 131
Barone V.Cossi M. J. Phys. Chem. A. 1998, 120: 1995 - 132
Mucsi Z.Szabó A.Hermecz I.Kucsman Á.Csizmadia IG. J. Am. Chem. Soc. 2005, 127: 7615 - 133
Wulf ORUL.Hendericks SB. J. Am. Chem. Soc. 1936, 58: 2287 - 134
Tamres M. J. Am. Chem. Soc. 1952, 74: 3375 - 135
Burkley SK.Petsko GA. Adv. Protein Chem. 1988, 39: 125 - 136
Steiner T. Acta Crystallogr., Sect. D 1998, 54: 584 - 137
Steiner T.Koellner G. J. Mol. Biol. 2001, 305: 535 - 138
Duan G.Smith VH.Weaver DF. Chem. Phys. Lett. 1999, 310: 323 - 139
Duan G.Smith VH.Weaver DF. Int. J. Quantum Chem. 2000, 80: 44 - 140
Bader RFW. Acc. Chem. Res. 1985, 18: 9 - 141
Bader RFW. Atoms in Molecules, A Quantum Theory Clarendon Press; Oxford UK: 1990. - 142
Matta CF.Hernandez-Trujillo J.Tang T.-H.Bader RFW. Chem. Eur. J. 2003, 9: 1940 - 143
Popelier PLA. J. Phys. Chem. A 1998, 102: 1873 - 144
Bader RFW.Fang D.-C. J. Chem. Theory Comput. 2005, 1: 403 - 145
Platts JA.Howard ST.Bracke BRF. J. Am. Chem. Soc. 1996, 118: 2726 - 146
Platts JA.Howard ST. J. Chem. Phys. 1996, 105: 4668 - 147
Koch U.Popelier PLA. J. Phys. Chem. 1995, 99: 9747 - 148
Gatti C.Saunders VR.Roetti C. J. Chem. Phys. 1994, 101: 10686 - 149
Espinosa E.Molins E.Lecomte C. Chem. Phys. Lett. 1998, 285: 170 - 150
Espinosa E.Souhassou M.Lachekar H.Lecomte C. Acta Crystallogr., Sect. B 1999, 55: 563 - 151
Rendeif EE.Dahaoui S.Renali-Cherif N.Lecomte C. Acta Crystallogr., Sect. B 2007, 63: 448 - 152
Albert S.Pillet S.Lecomte C.Pradel A.Ribes M. Acta Crystallogr., Sect. B 2008, 64: 1 - 153
Aubert E.Lecomte C. J. Appl. Crystallogr. 2007, 40: 1153 - 154
Koritsansky TS.Coppens P. Chem. Rev. 2001, 101: 1583 - 155
Flaig R.Koritsanszky TS.Dittrich B.Wagner A.Luger P. J. Am. Chem. Soc. 2002, 124: 3407 - 156
Lee C.-R.Tang T.-H.Chen L.Wang Y. Chem. Eur. J. 2003, 9: 3112 - 157
Guillot B.Jelsch C.Podjarny A.Lecomte C. Acta Crystallogr., Sect. D 2008, 64: 567 - 158
Tang T.-H.Deretey E.Knak Jensen SJ.Csizmadia IG. Eur. Phys. J., D: Atom Mol. Opt. Phys. 2006, 37: 217 - 159
Cortes-Guzman F.Richard RFW. Coord. Chem. Rev. 2005, 249: 633